2-(ortho-benzylbenzyl)-imidazoline and acid addition salts



2-(ORTHO-BENZYLBENZYL)-IMIDAZOLINE AND ACID ADDITION SALTS Merrill Eugene Specter, Kalamazoo, Mich., assignor to Bristol Laboratories Inc., Syracuse, N. Y., a corporation of New York No Drawing. Application June 27, 1955, Serial No. 518,352

3 Claims. (Cl. 260309.6)

%NCH1 CHr-C R NH H:

where R is benzyl.

The acid addition salts of this compound are also included within the present invention. Some examples of the non-toxic acid addition salts of the free base with inorganic or organic acids which may be prepared by the methods hereinafter described are the hydrochloride, hydrobromide, hydroiodide, sulfate, phosphate, maleate, acetate, citrate, oxalate, succinate, benzoate, tartrate, and the like.

z The compounds of this invention are also useful for their ability to decrease blood pressure.

The following example will serve to illustrate the invention without limiting it thereto:

Example Z-(ortho-benzylbenzyl) -imidazoline is prepared by heating 20' grams (0.084 mole) of methyl orthobenzylphenyl acetate for thirty hours on a steam bath with 18 grams (0.3 mole) of anhydrous ethylenediamine. The mixture was heated under vacuum and when the temperature of the bath reached 200 C., vapor was given oil and the vacuum fell considerably. After ten minutes the vacuum again reached 3 mm. and the temperature of the bath could be slowly raised without loss of vacuum. On distillation a main fraction boiling at 210280 C. The distillate solidified and the solid was thereafter dissolved in isopropanol and saturated with dry hydrogen chloride in the cold. The crystals, which formed and slowly separated, were filtered and again crystallized from isopropanol. The crystalline product melted at 172174 C., the yield thereof being 8 grams.

Analysis.Calculated for CrzHmNz HCI.

Calculated Found hydrochloride.

N 0 references cited. 

1. A COMPOUND SELECTED FROM THE GROUP CONSISTING OF 2-(ORTHO-BENZYLBENZYL)-IMIDAZOLINE AND ACID ADDITION SALTS THEREOF. 